US5124160A - Granulation of active ingredients using polyvinyl acetate and alcohol - Google Patents

Granulation of active ingredients using polyvinyl acetate and alcohol Download PDF

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Publication number
US5124160A
US5124160A US07/633,395 US63339590A US5124160A US 5124160 A US5124160 A US 5124160A US 63339590 A US63339590 A US 63339590A US 5124160 A US5124160 A US 5124160A
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United States
Prior art keywords
active ingredient
alcohol
granulation
polyvinyl acetate
granulated
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Expired - Lifetime
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US07/633,395
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English (en)
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Steven E. Zibell
Kevin B. Broderick
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WM Wrigley Jr Co
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WM Wrigley Jr Co
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Assigned to WM. WRIGLEY JR. COMPANY, A CORP. OF DE reassignment WM. WRIGLEY JR. COMPANY, A CORP. OF DE ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: BRODERICK, KEVIN B., ZIBELL, STEVEN E.
Priority to US07/633,395 priority Critical patent/US5124160A/en
Priority to FI915839A priority patent/FI915839A/fi
Priority to AU89645/91A priority patent/AU641111B2/en
Priority to CA002057658A priority patent/CA2057658A1/fr
Priority to EP91311792A priority patent/EP0492980A1/fr
Publication of US5124160A publication Critical patent/US5124160A/en
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Assigned to GOLDMAN SACHS CREDIT PARTNERS L.P., AS COLLATERAL AGENT reassignment GOLDMAN SACHS CREDIT PARTNERS L.P., AS COLLATERAL AGENT SECURITY AGREEMENT Assignors: WM WRIGLEY JR. COMPANY
Assigned to COOPERATIEVE CENTRALE RAIFFEISEN-BOERENLEENBANK B.A., "RABOBANK NEDERLAND", NEW YORK BRANCH, AS ADMINISTRATIVE AGENT reassignment COOPERATIEVE CENTRALE RAIFFEISEN-BOERENLEENBANK B.A., "RABOBANK NEDERLAND", NEW YORK BRANCH, AS ADMINISTRATIVE AGENT SECURITY AGREEMENT Assignors: WM. WRIGLEY JR. COMPANY
Anticipated expiration legal-status Critical
Assigned to WM. WRIGLEY JR. COMPANY reassignment WM. WRIGLEY JR. COMPANY SECURITY AGREEMENT Assignors: GOLDMAN SACHS CREDIT PARTNERS L.P.
Assigned to WM. WRIGLEY JR. COMPANY reassignment WM. WRIGLEY JR. COMPANY RELEASE BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: COOPERATIEVE CENTRALE RAIFFEISEN-BOERENLEENBANK B.A., "RABOBANK NEDERLAND", NEW YORK BRANCH, AS COLLATERAL AGENT
Expired - Lifetime legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A23G4/10—Chewing gum characterised by the composition containing organic or inorganic compounds characterised by the carbohydrates used, e.g. polysaccharides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/18—Chewing gum characterised by shape, structure or physical form, e.g. aerated products
    • A23G4/20—Composite products, e.g. centre-filled, multi-layer, laminated
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/20—Agglomerating; Granulating; Tabletting
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2/00—Processes or devices for granulating materials, e.g. fertilisers in general; Rendering particulate materials free flowing in general, e.g. making them hydrophobic
    • B01J2/28—Processes or devices for granulating materials, e.g. fertilisers in general; Rendering particulate materials free flowing in general, e.g. making them hydrophobic using special binding agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S426/00—Food or edible material: processes, compositions, and products
    • Y10S426/804—Low calorie, low sodium or hypoallergic

Definitions

  • the present invention relates to a method for granulating active ingredients for use in oral compositions, including chewing gum. More particularly, the present invention relates to a granulation which includes polyvinyl acetate, alcohol, and a modified cellulosic.
  • Fluid bed coating, fiber spinning, and spray drying are methods known in the art. These methods are designed to coat and protect the ingredient so there is prolonged release of sweetener or flavor as opposed to an overpowering initial release.
  • Another method involves granulating or agglomerating ingredients into a granular matrix which also provides for a more controlled release of ingredient.
  • PVAc polyvinyl acetate
  • One embodiment of the present invention is a method for granulating active ingredients for use in oral compositions.
  • the active ingredients are granulated or agglomerated as follows.
  • a quantity of granulating fluid comprising polyvinyl acetate (“PVAc”) dissolved in alcohol is added to powdered active ingredients and a modified cellulosic to form a damp granulation.
  • the damp granulation is dried until hardened, and ground to a desired particle size.
  • the particles of granulated active ingredient are then incorporated into an oral composition formulation.
  • Another embodiment of the present invention is a method for preparing chewing gum and other oral compositions containing granulated active ingredients.
  • Another embodiment of the present invention is a granulating fluid comprising polyvinyl acetate and alcohol.
  • Another embodiment of the present invention is a granulation comprising polyvinyl acetate, alcohol, and modified cellulosic.
  • Another embodiment of the present invention is a granulated active ingredient comprising polyvinyl acetate, modified cellulosic, and active ingredient.
  • a further embodiment of the present invention is a chewing gum composition that includes gum base, softener, sweetener, and granulated active ingredient.
  • the present invention is advantageous in that it achieves a highly desirable active ingredient release over at least ten minutes.
  • the granular matrix is a support matrix through which granulated active ingredients may be released gradually and continuously.
  • the granular matrix also reduces the surface area of granulated active ingredients exposed to solvents.
  • active ingredient as used herein is intended to refer to various types of sweeteners, salts, food acids, and medicaments.
  • active ingredients include, but are not limited to, high intensity sweeteners such as aspartame, alitame, acesulfame-K, Sucralose®, saccharin and its salts, cyclamic acid and its salts, dihydrochalones, thaumatin, monellin and glycyrrhizan and its acid and salt forms, salts such as sodium chloride and potassium chloride, and food acids such as adipic, malic, citric, and fumaric acid.
  • high intensity sweeteners such as aspartame, alitame, acesulfame-K, Sucralose®, saccharin and its salts, cyclamic acid and its salts, dihydrochalones, thaumatin, monellin and glycyrrhizan and its acid and salt forms
  • salts such as sodium chloride and potassium
  • FIG. 1 shows a schematic representation of a preferred method of the present invention.
  • FIG. 2 shows a graph illustrating the release profile of a granulated sweetener in chewing gum.
  • the present invention is a method for granulating active ingredients.
  • This method utilizes a granulation comprising polyvinyl acetate, alcohol and a modified cellulosic.
  • the granulation is mixed with an active ingredient, dried, and particle-sized to produce granulated active ingredient.
  • FIG. 1 is a diagram illustrating the steps in the method of one of the preferred embodiments of the present invention.
  • a granulating fluid is prepared by dissolving low molecular weight PVAc (approximately 10,000-20,000 MWU) in alcohol.
  • the granulating agent PVAc is not water soluble but is soluble in an alcohol solvent.
  • the alcohol is methanol, ethanol, or a combination thereof.
  • the PVAc and alcohol are combined in a 1:1 ratio and heated until the PVAc is dissolved. It is most desirable to heat the mixture to 120° F. (49° C.) for approximately 1.5 hours.
  • the granulating fluid is then gradually added to a powdered mixture of ingredients which include a modified cellulosic and an active ingredient to form a granulation.
  • the preferred modified cellulosic for use in the granulation is ethylcellulose.
  • Ethylcellulose is derived from cellulose, a naturally-occurring polymer, and aids in binding the active ingredient as well as in controlling the release of the active ingredient.
  • Ethylcellulose is particularly useful in the present invention because it is soluble in alcohol and is a desirable granulating agent for use in oral compositions. It is colorless, odorless, and tasteless.
  • Ethocel® is added to the granulation.
  • the use of other modified cellulosics is also contemplated.
  • the amount of modified cellulosic added to the granulation is about 5% to about 40%. Most preferably, the amount of modified cellulosic added is about 15% to about 30%.
  • the active ingredients added to the granulation of the present invention include but are not limited to sweeteners, salts, food acids, and medicaments.
  • these active ingredients are high intensity sweeteners such as aspartame, alitame, acesulfame-K, Sucralose®, saccharin and its salts, cyclamic acid and its salts, dihydrochalones, thaumatin, monellin, and glycyrrhizan and its acid and salt forms, salts such as sodium chloride and potassium chloride, and food acids such as adipic, malic, citric, and fumaric acid.
  • high intensity sweeteners such as aspartame, alitame, acesulfame-K, Sucralose®, saccharin and its salts, cyclamic acid and its salts, dihydrochalones, thaumatin, monellin, and glycyrrhizan and its acid and salt forms
  • salts such as sodium chloride and
  • the active ingredient is a high intensity sweetener.
  • Example I describes a method for granulating the high intensity sweetener, Sucralose®.
  • the granulated active ingredient is a salt.
  • Example II describes a method for preparing granulated sodium chloride.
  • the active ingredient is generally about 25% to about 85% of the granulation.
  • the active ingredient added is about 40% to about 70%.
  • the granulating fluid, modified cellulosic, and active ingredient are mixed until homogenous and a damp, dust-free, and crumbly mixture is formed.
  • the optimum time for mixing can be determined visually. At this stage, the granulation should coalesce when pressed together.
  • the granulation is dried to remove all traces of the alcohol solvent.
  • the granulation is removed from the mixing bowl and spread onto trays prior to drying. Drying is most preferably accomplished by heating the granulation in a convection oven for about 24 hours.
  • the granulation is generally characterized as being in the form of hard, dry lumps of various sizes and shapes.
  • the dried granulation is then ready to be ground to the desired range of particle sizes of granulated active ingredient. This can be accomplished is several ways. Most preferably, the dried granulation is fed into a cryogenic grinder which comminutes it into smaller particles.
  • the grinder or other device used is preferably equipped with a screen which will pass the desired particle range. Desired particle size ranges of the present invention are about 0.0001" to about 0.1". Preferably, the particle size ranges from about 0.0017" (325 mesh) to about 0.0165" (40 mesh) when added to a chewing gum formulation.
  • the particle-sized, granulated active ingredient is then ready for incorporation into formulations for oral compositions.
  • the granulated active ingredient is added to a chewing gum composition.
  • the preferred chewing gum composition is a sugar-sweetened chewing gum to intensify and extend the sweetness and flavor thereof.
  • the present invention may also be used in a sugarless gum to intensify and extend the sweetness thereof.
  • the granulated active ingredient is added to a chewing gum formulation early in the mixing process.
  • Optimum levels of granulated active ingredient may vary from about 0.1% to about 3% in a chewing gum formulation.
  • the level of granulated active ingredient added is about 0.5% to about 1.5%.
  • the present invention is not limited to these approximate ranges of granulated active ingredient added to chewing gum formulations. The level of granulated active ingredient added will depend upon the final concentration of the active ingredient in the granulation.
  • a chewing gum comprises a water-soluble bulk portion, a water-insoluble chewable gum base portion and typically, water-insoluble flavor ingredients.
  • the water-soluble portion dissipates with a portion of the flavor over time during chewing.
  • the gum base portion is retained in the mouth throughout the chew.
  • the insoluble gum base generally comprises elastomers, resins, fats and oils, waxes, softeners and inorganic fillers.
  • the insoluble gum base constitutes between about 5% to about 95% of the gum, and more preferably about 20% to about 30%.
  • the gum base typically also includes a filler component.
  • the filler component may be calcium carbonate, magnesium carbonate, talc, dicalcium phosphate, and the like.
  • the filler may constitute between about 5% to about 60% of the gum base.
  • the filler comprises about 5% to about 50% of the chewing gum base.
  • the gum base also contains softeners, including glycerol monostearate and glycerol triacetate.
  • gum bases may also contain additional ingredients such as anti-oxidants, colors, and emulsifiers. The present invention contemplates using any commercially acceptable gum base.
  • the water-soluble portion of chewing gum may further comprise softeners, sweeteners, and flavors and combinations thereof.
  • the softeners are added to the chewing gum in order to optimize the chewing ability and mouth feel of the gum.
  • Softeners also known in the art as plasticizers, generally constitute about 0.1% to about 15% of the chewing gum.
  • Softeners contemplated by the present invention include glycerin, lecithin and combinations thereof.
  • Aqueous sweetener solutions such as those containing sorbitol, hydrogenated starch hydrolysates, corn syrup, and combinations thereof may be used as softeners and binding agents in gum.
  • Sweeteners contemplated by the present invention for use in chewing gum include both sugar and sugarless components.
  • Sugar sweeteners generally include saccharide-containing components commonly known in the art and include, but are not limited to, sucrose, dextrose, maltose, dextrin, dried invert sugar, fructose, levulose, galactose, corn syrup solids and the like, alone or in any combination.
  • Sugarless sweeteners include components with sweetening characteristics but are devoid of the commonly known sugars and comprise, but are not limited to, sugar alcohols such as sorbitol, mannitol, xylitol, hydrogenated starch hydrolysates, maltitol, and the like, alone or in any combination.
  • high intensity sweeteners such as aspartame, Sucralose®, cyclamate, acesulfame-K, dihydrochalones, alitame, and saccharin.
  • any combination of sugar/sugarless sweeteners may be employed in the chewing gum.
  • a sweetener may be present in a chewing gum in whole or in part as a water-soluble bulking agent, and that the softener may be combined with a sweetener such as an aqueous sweetener solution.
  • the granulated active ingredients in the present invention may also be used in combination with ingredients which are not granulated, coated, or encapsulated, or with ingredients granulated, coated, or encapsulated with other materials or other methods.
  • a flavoring agent may be present in the chewing gum in an amount from about 0.1% to about 10.0% and preferably from about o.5% to about 3% of the gum.
  • Flavoring agents may comprise essential oils, synthetic flavors, or mixtures thereof including but not limited to oils derived from plants and fruits such as citrus oils, fruit essences, peppermint oil, spearmint oil, clove oil, oil of wintergreen, anise and the like. Artificial flavoring components are also contemplated. Those skilled in the art will recognize that natural and artificial flavoring agents may be combined in any sensorially acceptable blend. All such flavors and flavor blends are contemplated by the present invention.
  • chewing gum is manufactured by sequentially adding the various chewing gum ingredients to any commercially available mixer known in the art. After the ingredients have been thoroughly mixed, the gum mass is discharged from the mixer and shaped into the desired forms such as by rolling into sheets and cutting into sticks, extruding into chunks, or casting into pellets.
  • the ingredients are mixed by first melting the gum base and adding it to the running mixer. The base may also be melted in the mixer itself. Color may also be added at this time. A softener such as glycerin may then be added next along with the syrup and a portion of bulking agent. Further portions of the bulking agents may be added to the mixer.
  • the flavor ingredients are added to the gum mixture near the end of the mixing process. The entire mixing procedure takes from about 5 minutes to 15 minutes, however, longer mixing times may be required. Those persons skilled in the art will recognize that many variations of the above described procedure may be followed.
  • the granulated active ingredient may be added to other oral compositions such as pharmaceuticals.
  • the granulated active ingredient comprises about 0.1% to about 3% of the oral composition.
  • a granulating fluid was prepared by dissolving low molecular weight PVAc in methanol (MeOH) at a 1:1 ratio. The mixture was heated to 120° F. (49° C.) for approximately 1.5 hours until the PVAc was completely dissolved.
  • a granulation containing the high intensity sweetener, Sucralose® was prepared as follows and included the ingredients below:
  • ethylcellulose and Sucralose® were placed in a mixing bowl.
  • the granulating fluid was added slowly to these ingredients during mixing until the composition became homogeneous, damp, and crumbly.
  • the damp granulation was spread onto a tray and heated gently for 24 hours in a convection oven to remove all traces of the alcohol solvent.
  • the hard, dried granulation was particle-sized with a grinder to produce particles of granulated sweetener of about 0.05" in size.
  • a granulated active ingredient was prepared as described in Example 1 except that the active ingredient added to the granulation was the salt, sodium chloride.
  • the granulation comprised the following formula:
  • Example 2 Two laboratory-scale batches of chewing gum were prepared and evaluated by trained panelists.
  • the particle-sized, granulated sweetener described in Example 1 was added to a spearmint-flavored chewing gum formulation with the ingredients, weight percentages, and mixing schedule listed below:
  • the above ingredients were added into the gum mixture at the time indicated in the mixing schedule.
  • the total mixing time was ten minutes.
  • the gum was then rolled out and cut into uniform pieces for testing.
  • the control batch of chewing gum was prepared in the same manner except that 53.7% sugar was added, and 0.06% neat Sucralose® was added instead of 0.11% granulated Sucralose®.
  • the two batches of chewing gum were evaluated by sensory testing of four trained panelists. Panelists reported flavor and sweetness release by a rating of high, moderate, low, and nothing at various intervals for 10 minutes. A rating of "high+” indicated a most intense sweetness, and a rating of "nothing” indicated no sweetness was perceptible. The results are shown in FIG. 2.
  • the panelists unexpectedly experienced moderate sweetness in the experimental gum as long as 10 minutes. This is exceptionally long lasting sweetness as compared to the control chewing gum that received a low rating as early as 4 minutes.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Inorganic Chemistry (AREA)
  • Confectionery (AREA)
  • Medicinal Preparation (AREA)
US07/633,395 1990-12-21 1990-12-21 Granulation of active ingredients using polyvinyl acetate and alcohol Expired - Lifetime US5124160A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US07/633,395 US5124160A (en) 1990-12-21 1990-12-21 Granulation of active ingredients using polyvinyl acetate and alcohol
FI915839A FI915839A (fi) 1990-12-21 1991-12-11 Granulering av aktiva bestaondsdelar medelst anvaendning av polyvinylacetat och alkohol.
AU89645/91A AU641111B2 (en) 1990-12-21 1991-12-11 Granulation of active ingredients using polyvinyl acetate and alcohol
CA002057658A CA2057658A1 (fr) 1990-12-21 1991-12-13 Granulation d'ingredients actifs au moyen d'alcool et d'acetate de polyvinyle
EP91311792A EP0492980A1 (fr) 1990-12-21 1991-12-19 Granulation de substances actives au moyen d'acétate de polyvinyl et d'alcool

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Application Number Priority Date Filing Date Title
US07/633,395 US5124160A (en) 1990-12-21 1990-12-21 Granulation of active ingredients using polyvinyl acetate and alcohol

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US5124160A true US5124160A (en) 1992-06-23

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US (1) US5124160A (fr)
EP (1) EP0492980A1 (fr)
AU (1) AU641111B2 (fr)
CA (1) CA2057658A1 (fr)
FI (1) FI915839A (fr)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5227182A (en) * 1991-07-17 1993-07-13 Wm. Wrigley Jr. Company Method of controlling release of sucralose in chewing gum using cellulose derivatives and gum produced thereby
US5433960A (en) * 1992-04-21 1995-07-18 Wm. Wrigley Jr. Company Chewing gum including agent containing edible film
US5645853A (en) * 1995-08-08 1997-07-08 Enamelon Inc. Chewing gum compositions and the use thereof for remineralization of lesions in teeth
US5792495A (en) * 1996-10-03 1998-08-11 Warner-Lambert Company Elastomer processing system for chewing gum
US5833957A (en) * 1995-08-08 1998-11-10 Enamelon, Inc. Processes and compositions for the remineralization of teeth
US5837302A (en) * 1996-10-03 1998-11-17 Warner-Lambert Company Polyvinyl acetate process for chewing gum
US5895641A (en) * 1995-06-06 1999-04-20 Enamelon Processes and composition for remineralization and prevention of demineralization of dental enamel
US5958380A (en) * 1997-07-07 1999-09-28 Enamelon, Inc. Chewing gum products and the use thereof for remineralizing subsurface dental lesions and for mineralizing exposed dentinal tubules
US6159449A (en) * 1997-04-03 2000-12-12 Enamelon, Inc. Dentifrice products and methods for remineralizing and/or mineralizing teeth
US6159448A (en) * 1996-09-27 2000-12-12 Enamelon, Inc. Products and methods for the remineralization and prevention of demineralization of teeth
WO2001049124A1 (fr) 1999-12-30 2001-07-12 Wm. Wrigley Jr. Company Chewing gum a liberation de principes actifs lipophiles
US6451290B2 (en) 1996-09-27 2002-09-17 Church & Dwight Co., Inc. Products and methods for the remineralization and prevention of demineralization of teeth
US6630182B1 (en) 1997-12-30 2003-10-07 Cadbury Adams Usa Llc System for continuously producing gum with improved texture and flavor release
US20090280211A1 (en) * 2006-05-17 2009-11-12 Friedman Robert B Method of preparing a food product

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Publication number Priority date Publication date Assignee Title
WO2000019977A1 (fr) * 1998-10-08 2000-04-13 Biovail Technologies Ltd. Composition et procede d'un systeme d'administration de chewing gum medicamenteux

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US3795744A (en) * 1970-10-21 1974-03-05 Lotte Co Ltd Flavor variable chewing gum and methods of preparing the same
US3826847A (en) * 1970-10-21 1974-07-30 Lotte Co Ltd Process for preparation of flavor durable chewing gum
US4992280A (en) * 1989-12-18 1991-02-12 Columbia Laboratories, Inc. Sustained flavorant release composition, method for making same and chewable structure incorporating same

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US4981698A (en) * 1986-12-23 1991-01-01 Warner-Lambert Co. Multiple encapsulated sweetener delivery system and method of preparation
EP0320522B1 (fr) * 1987-12-15 1992-01-22 Wm. Wrigley Jr. Company Méthode pour préparer des produits à libération contrôlée pour gomme à mâcher
WO1990007859A2 (fr) * 1989-11-22 1990-07-26 Wm. Wrigley Jr. Company Procede de regulation de liberation de sucralose dans une gomme a macher et gomme ainsi produite

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US3795744A (en) * 1970-10-21 1974-03-05 Lotte Co Ltd Flavor variable chewing gum and methods of preparing the same
US3826847A (en) * 1970-10-21 1974-07-30 Lotte Co Ltd Process for preparation of flavor durable chewing gum
US4992280A (en) * 1989-12-18 1991-02-12 Columbia Laboratories, Inc. Sustained flavorant release composition, method for making same and chewable structure incorporating same

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5227182A (en) * 1991-07-17 1993-07-13 Wm. Wrigley Jr. Company Method of controlling release of sucralose in chewing gum using cellulose derivatives and gum produced thereby
WO1993017569A1 (fr) * 1992-03-02 1993-09-16 Wm. Wrigley Jr. Company Regulation de la liberation de sucralose dans des chewing-gums au moyen de derives cellulosiques et chewing-gum
US5433960A (en) * 1992-04-21 1995-07-18 Wm. Wrigley Jr. Company Chewing gum including agent containing edible film
US5895641A (en) * 1995-06-06 1999-04-20 Enamelon Processes and composition for remineralization and prevention of demineralization of dental enamel
US5645853A (en) * 1995-08-08 1997-07-08 Enamelon Inc. Chewing gum compositions and the use thereof for remineralization of lesions in teeth
US5833957A (en) * 1995-08-08 1998-11-10 Enamelon, Inc. Processes and compositions for the remineralization of teeth
US6451290B2 (en) 1996-09-27 2002-09-17 Church & Dwight Co., Inc. Products and methods for the remineralization and prevention of demineralization of teeth
US6159448A (en) * 1996-09-27 2000-12-12 Enamelon, Inc. Products and methods for the remineralization and prevention of demineralization of teeth
US6168306B1 (en) 1996-10-03 2001-01-02 Warner-Lambert Company Adapter member for connecting extruders
US5792495A (en) * 1996-10-03 1998-08-11 Warner-Lambert Company Elastomer processing system for chewing gum
US5837302A (en) * 1996-10-03 1998-11-17 Warner-Lambert Company Polyvinyl acetate process for chewing gum
US5944266A (en) * 1996-10-03 1999-08-31 Degady; Marc Elastomer processing apparatus and system for chewing gum
US6159449A (en) * 1997-04-03 2000-12-12 Enamelon, Inc. Dentifrice products and methods for remineralizing and/or mineralizing teeth
US5958380A (en) * 1997-07-07 1999-09-28 Enamelon, Inc. Chewing gum products and the use thereof for remineralizing subsurface dental lesions and for mineralizing exposed dentinal tubules
US6630182B1 (en) 1997-12-30 2003-10-07 Cadbury Adams Usa Llc System for continuously producing gum with improved texture and flavor release
US20040067278A1 (en) * 1997-12-30 2004-04-08 Warrington Richard Mark System for continuously producing gum with improved texture and flavor release
WO2001049124A1 (fr) 1999-12-30 2001-07-12 Wm. Wrigley Jr. Company Chewing gum a liberation de principes actifs lipophiles
EP1241949A1 (fr) * 1999-12-30 2002-09-25 Wm. Wrigley Jr. Company Chewing gum a liberation de principes actifs lipophiles
EP1241949A4 (fr) * 1999-12-30 2004-12-08 Wrigley W M Jun Co Chewing gum a liberation de principes actifs lipophiles
US20090280211A1 (en) * 2006-05-17 2009-11-12 Friedman Robert B Method of preparing a food product

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AU8964591A (en) 1992-06-25
FI915839A (fi) 1992-06-22
AU641111B2 (en) 1993-09-09
CA2057658A1 (fr) 1992-06-22
FI915839A0 (fi) 1991-12-11
EP0492980A1 (fr) 1992-07-01

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